Beyond Orders

In this episode of Beyond Orders, I sit down with Lauren Cecora -  a 16-year Air Force spouse, devoted mom of two daughters, homeschool parent, and author of Past-Partum. Lauren opens up about the challenges and triumphs of military family life, from navigating deployments to preparing for her husband’s upcoming retirement after nearly two decades of service.

We dive into her journey through postpartum struggles and how sharing her...

In this episode of Beyond Orders, we sit down with Kerissa Frigo. Veteran, military spouse, mom of two energetic boys, and now an Executive Assistant with Squared Away.

Kerissa shares her journey from serving five years in the Air National Guard to navigating a decade of marriage through the highs and lows of military life. She opens up about raising a child with Williams Syndrome and how that experience has reshaped her outlook on...

In this episode of Beyond Orders, we sit down with Danielle Hillebrand, a professional body piercer with 17 years of experience and a proud military spouse of 8 years. Danielle’s story is one of resilience, reinvention, and the relentless pursuit of identity in the face of constant transition.

Each PCS move has brought new challenges, but also new opportunities. Danielle has successfully restarted her studio, Elegant Edge, four tim...

Taylor Lingerfelt is a proud active duty Army spouse, mom of two, and Team Lead at Squared Away. She began her journey with the company in 2021 while at home with her kids, seeking a way to reconnect with her own identity. Over the years, she’s held multiple internal roles, growing her skills in leadership, client success, and remote team management. Today, Taylor is passionate about finding balance between family life and career, ...

This week on Beyond Orders, we sit down with Libby Jamison, a powerhouse attorney, policy strategist, and unapologetic advocate for military families. With nearly 20 years in law, government, and grassroots organizing, Libby has worked everywhere from the Department of Veterans Affairs to the West Wing, where she served as Senior Advisor to Joining Forces, Dr. Jill Biden’s initiative supporting military families, caregivers, and su...

Meagan Eskew started as a virtual assistant with Squared Away in 2020 and worked her way up to become our Director of Client Connections. A single mom who battled, and beat, breast cancer, Meagan didn’t just climb the ladder, she built her own. Now, she’s stepping into a full-time role with a client buyout, proving what happens when grit meets opportunity.

She homeschools her kids, leads with heart, and shows exactly what betting o...

What does it take to grow from a virtual assistant to a trusted executive leader, all while proving that military spouses are some of the strongest leaders in the workforce?

In this episode of Beyond Orders, Michelle Penczak, CEO of Squared Away, interviews Jessica Ryan, the company’s Chief People Officer. Jessica started in 2020 as a virtual assistant and steadily rose through the ranks, from Team Lead to the executive team, by le...

In this episode of Beyond Orders, host Michelle Penczak, CEO of Squared Away and military spouse, sits down with Sara Brooks-Glover, Chief Operations Officer at Squared Away, to talk about career growth, remote leadership, and scaling systems in a mission-driven company.

Sara shares her inspiring journey from starting as a virtual assistant to rising through the ranks as Director of Finance and Compliance, leading Talent and Develo...

In this deeply moving episode of Beyond Orders, host Michelle Penczak sits down with Tiffany McCawley, a military spouse and mother of five whose faith and resilience leave a lasting impression. Tiffany became part of the Squared Away team in 2020, but her journey began long before that.

In 2015, Tiffany endured every parent’s worst nightmare; the loss of two of her children in a tragic accident. What followed was not a neatly wrap...

In this episode of Beyond Orders, host Michelle Penczak speaks with Rachel Hornbeck, the Director of Talent and Development at Squared Away, about her journey from being a stay-at-home mom to a leadership role within the company. They discuss the supportive culture at Squared Away, the challenges of imposter syndrome, the importance of community, and the personal stories of adoption that have shaped their lives. Rachel shares her i...

In the inaugural episode of Beyond Orders, host Michelle Penczak sits down with Jordan Streetman Cole, Chief Experience Officer at Squared Away, for a powerful conversation about the realities of military spouse life and the unexpected opportunities that can come from uncertainty.

Together, they unpack Jordan’s journey from applying to Squared Away out of sheer desperation to growing into a key leadership role within the company. A...